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Proxymetacaine

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(Redirected from Proparacaine) Chemical compound Pharmaceutical compound
Proxymetacaine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Topical (eye drops)
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
Pharmacokinetic data
MetabolismPlasma
Identifiers
IUPAC name
  • 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.169 Edit this at Wikidata
Chemical and physical data
FormulaC16H26N2O3
Molar mass294.395 g·mol
3D model (JSmol)
SMILES
  • O=C(OCCN(CC)CC)c1ccc(OCCC)c(c1)N
InChI
  • InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
  • Key:KCLANYCVBBTKTO-UHFFFAOYSA-N
  (verify)

Proxymetacaine (INN) or proparacaine (USAN) is a topical anesthetic drug of the aminoester group.

Clinical pharmacology

Proxymetacaine is a local anesthetic which on topical application penetrates sensory nerve endings in the corneal tissue.

Mechanism of action

Proxymetacaine is believed to act as an antagonist on voltage-gated sodium channels to affect the permeability of neuronal membranes; how this inhibits pain sensations and the exact mechanism of action of proxymetacaine are, however, unknown.

Indications and usage

Proxymetacaine hydrochloride ophthalmic solution (eye drops) is indicated for procedures such as tonometry, gonioscopy, removal of foreign bodies, or other similar procedures requiring topical anesthesia of the cornea and conjunctiva.

Warnings

Proxymetacaine is for topical ophthalmic use only, and it is specifically not intended for injection. Prolonged use of this or any other topical ocular anesthetic may produce permanent corneal opacification with accompanying visual loss.

How supplied

Proxymetacaine is available as its hydrochloride salt in ophthalmic solutions at a concentration of 0.5%. Although it is no longer on patent, it is still marketed under the trade names Alcaine, Ak-Taine, and others. Proparacaine 0.5% is marketed as Poencaina by Poen Laboratories.

References

  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. Draeger J, Langenbucher H, Bannert C (1984). "Efficacy of topical anaesthetics". Ophthalmic Research. 16 (3): 135–8. doi:10.1159/000265308. PMID 6472792.
  3. Goodman LS, Gilman AG, Goodman A (1980). The Pharmacological Basis of Therapeutics (6th ed.). New York: MacMillan Pub. ISBN 978-0023447204.
  4. Murphy PJ, Ntola AM (April 2009). "Prolonged corneal anaesthesia by proxymetacaine hydrochloride detected by a thermal cooling stimulus". Contact Lens & Anterior Eye. 32 (2): 84–7, quiz 99–100. doi:10.1016/j.clae.2008.12.006. PMID 19181566.
  5. "Poen-Caina generic. Price of poen-caina. Uses, Indications and Description". ndrugs. Retrieved 15 March 2018.
Local anesthetics (primarily sodium channel blockers) (N01B)
Esters by acid
Aminobenzoic
Benzoic
ArCO2- (not para-amino or Ph)
Amides
Combinations
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